Travel to the Leeward Islands of the Lesser Antilles in the Caribbean – Episode 386

categories: caribbean travel

Hear about travel to the Leeward Islands of the Lesser Antilles in the Caribbean as the Amateur Traveler talks again to Gary Arndt of

Gary just finished an island hopping tour that took him to most of the islands in the Caribbean. We will cover the islands of St. Martin, Anguilla, Saba, St. Barts, St. Eustatius, St. Kitts, Nevis, Antigua, Barbuda, and Montserrat on this episode.

Gary found wonderful beaches, coral atolls, rugged volcanic islands (one with an active volcano), rich histories, a variety of languages and cultures. He found that the low season (Summer in North America) was a great time to go to the Caribbean but he also found some difficulties in trying to cover as many islands as he did.

“Basically all of the islands [in the Caribbean] are within eyesight of another island. With the exception of Barbados and I think Trinidad you can always see the next islands you are going to. So they are very close. They may be as close as 20 miles or sometimes even less; however, that doesn’t mean that going between the islands is at all easy.”

“For starters, inter-island flights are pretty much a monopoly of an airline called LIAT which stands for Leeward Islands Air Transport but is also known as Leave Island Any Time, and Luggage In Another Terminal. I did a 26-minute flight from Tortola in the British Virgin Islands to St Martin in which my bag was lost. I had flights delayed for many many hours. What would end up being a 30-minute flight and you’re delayed 6 hours.”

“The ferry service between the islands doesn’t always make sense. A lot of times it is simply based on demand not necessarily distance. So you have things like St. Eustatius which is very close to St. Kitts but there is no ferry traffic in between them. The ferries, for the most part, ran on schedule although since Gary traveled in the low season they did not always run as often as they would in the high season.”

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Show Notes

Everything Everywhere
Leeward Islands
Caribbean Ferries
Bolongo Bay Beach Resort
Saint Martin
Princess Juliana International Airport
Maho Beach
Visit Anguilla
Savanna Bay
Saba Tourism
Mount Scenery
Saba Airport
St. Barts
F.D. Roosevelt Airport
St. Kitts
Brimstone Fortress
G Adventures
This Week In Travel


Flight diverted due to ‘smelly’ new carpet
Boobies get tourist board in trouble
Etihad to introduce ‘flying nannies’


Jaki on Travel to South Australia – Episode 377

Wayne writes:

Hi Chris, thanks for the name check the other week. I booked a San Diego dinner cruise with Viator and you mentioned it at the start of a show. Just to say the cruise was excellent, as was San Diego, which I know you are a fan of.

Not long back in the UK after 20 day in the US taking in Newport Beach (have relatives living there), San Diego, Palm Springs, Joshua Tree National Park, Roys Cafe at Amboy and a slice of Route 66, Las Vegas, Yosemite, San Francisco and the bay area (wife had a conference to attend at Berkeley) Santa Cruz and Monterey/Pacific Grove (where the other half of her conference was!). Had an excellent time and looking forward to coming back over the US in November to visit Florida’s Gulf coast and the Keys. Will have to have another look on Viator to see what happening in that vicinity.

Keep up the good work!
Many thanks


Chris: I’d like to welcome back to the show Gary Arndt from, who’s come to talk to us about his recent trip to the Caribbean, especially to the Leeward Islands. Gary, welcome back to the show.

Gary: Thanks for having me.

Chris: Now for some of us, at least two of us, this whole interview is going to sound very familiar because we had a technical problem and we’ve done this one before. So my apologies first to Gary, and thank you for your patience in coming back and doing this again with me in the course of two weeks.

Gary: That’s okay. It’s just when you count the number of times I’ve been in the show I would like half credit for previous attempt.

Chris: That seems completely reasonable. Gary, as we say, has been on the show before. He has been on the show talking about, and I’m not sure if I can do this in order, the Federated States of Micronesia, the Microstates of Europe, the UNESCO World Heritage Sites, the Canary Islands …

Gary: And the Gulf States.

Chris: … and the Gulf States, there we go.

Gary: So this is my sixth time on the show?

Chris: Or six and a half, if we …

Gary: Six and a half. Once again, we’re talking about little islands.

Chris: This does seem to be a theme with us. You recently finished a tour of much of the Caribbean all in one trip, and that is not a typical trip.

Gary: No. I started in June 2013 in the Bahamas and then worked my way from the U.S. Virgin Islands, British Virgin Islands, Saint Martin, Anguilla, Saba, Saint Eustatius, Saint Barts, Saint Kitts, Nevis, Anguilla, Antigua, Montserrat, Guadeloupe, Dominica, Martinique, Saint Lucia, Barbados, Saint Vincent, Grenada, and Trinidad.

Chris: We’re not going to try to do all of that in this episode, but we’re going to try to do about half. We’re going to do the Leeward Islands and we’ll save the Windward Islands for a later episode. Also you started in the Virgin Islands, which we’ve done some of already on the Amateur Traveler, so we’re going to focus a little to the east of the Virgin Islands.

Gary: Yeah. Just so your listeners know, the Caribbean is a lot of different islands and they’re broken up into different groups. Roughly speaking, there are two main groups, and they are the Bahamas and the Antilles. The Bahamas consists of the Nation of the Bahamas and the Turks and Caicos, and the Antilles is pretty much everything else. The Antilles are then split into two groups; the Greater Antilles, which are the big islands like Cuba, Haiti, Dominican Republic, Jamaica and also the Cayman Islands are included in that and Puerto Rico; and then the Lesser Antilles, which tend to be the smaller islands which are pretty much all the ones I just listed. And then, of the Lesser Antilles, those are split into two groups, which are the Leeward Islands and Windward Islands. The Leeward Islands are in the north and the Windward Islands are in the south.

Chris: It seems like the only ones you didn’t get to this time are the Greater Antilles and the Netherlands Antilles.

Gary: Technically speaking, the Netherlands Antilles no longer exists. They were dissolved in 2010. What you’re probably referring to are the ABC Islands of Aruba, Bonaire, and Curacao. I’ve been to those previously and those were usually lumped together with the Windward Islands as well, although they’re kind of off the archipelago. Yeah, I didn’t visit them on this trip because I’ve been there previously.

Chris: Excellent. Before we get into the specifics and I want to get and talk about a number of the different islands individually, but the overall trip I think you learned a couple of things, so most people are not going to be following you on this trip and it’s not as easy as you may have once thought.

Gary: No. Basically, all of the islands are within eyesight of another island. With the exception of Barbados and I think Trinidad, you can always see the next island you’re going to, so they’re very close, and then may be as close as 20 miles or sometimes even less. However, that doesn’t mean that going between the islands is at all easy. For starters, inter-island flights are pretty much a monopoly of an airline called LIAT, which stands for Leeward Island Air Transport, but is also known as Leave Island Any Time, Luggage In Another Terminal … I probably heard like five different acronyms for it.
The ferry service between the islands doesn’t always make sense, and a lot of times it’s simply based on demand, not necessarily distance, and so you have things like Saint Eustatius which is quite close to Saint Kitts, but there’s no ferry traffic between it even though Saint Eustatius is closer to Saint Kitts than Saint Martin, but there’s a ferry between Saint Martin and Saint Eustatius.

Chris: You ran into I think all of the problems you’re talking about. You ran into doing a really short flight and yet getting there without your luggage.

Gary: I did a 26-minute flight from the Tortola in the British Virgin Islands to Saint Martin, which my bag was lost; turns out they never put on the plane at all. I had flights delayed for many, many hours, what would end up being like a 30-minute flight and you’re delayed six hours. The ferries for the most part ran according to schedule. My trip there was in the low season, which is summer in North America, and so ferries often will not run as often as they do in the high season, so that was something to take into consideration as well.

Chris: It sounds like in general that being there in the low season actually worked out very well for you.

Gary: It’s not bad. People have the impression that it’s impressively hot, but quite frankly it’s not that much different than it is in the winter. There might be a bit more humidity, but I found looking at temperatures that it was actually cooler sometimes on the islands than it was in many large North American cities. It will seldom get oppressively hot, it will get very warm, but certainly not as bad as what you’re going to see in places like Phoenix for most of the summer.

Chris: Then the other things you ran into where bureaucratic red tape, although I think you ran into more of those in the Windward Islands, as I recall, the worst …

Gary: It’s a problem everywhere, simply because … and this goes back to the history of the islands that they were all colonized by either the French or the British for the most part. There were some Danish and Swedish involvement, but they eventually sold off to other European countries. When they decolonized, they fragmented into every island on its own, which is why you see so many different little countries, and to this day you’ll still see a fair number of small territories that are not really small enough to become independent countries or not large enough to become independent countries.

Chris: Let’s start doing the islands in order. You flew into …

Gary: St. Thomas, which should have been my first stop. Spent several days there and eventually took the ferry to Road Town in the British Virgin Islands. We’d spend a lot of time talking about the Virgin Islands, but suffice to say I think the British Virgin Islands are much more high ends than the U.S. Virgin Islands. A lot of people say that St. Thomas is the most developed, and they’re right, but it’s also the easiest accessible. Their port connects the plane from pretty much anywhere, so it’s a common entry point into the region.

Chris: It’s most accessible, too. It gets a lot of tourism. I think I have seen as many as four cruise ships in the harbor at the same time.

Gary: Yeah. I felt that the British Virgin Islands are much more laid back and just nicer. I should note if you do travel by ferry from U.S. to British Virgin Islands, expect to get far more scrutiny at the ferry terminal than you would have if you’re flying in. I was told that because there’s been drug smuggling between the islands and so they give you extra attention when you arrive.

Chris: Interesting. Then from the Virgin Islands, you went …

Gary: To Saint Martin, which is, if not the hub, one of the major hubs for the region along with Antigua. The island is flipped between the French and the Dutch side, so the French side is a part of France. The license plates are French license plates. They use the euro. It technically is France. Although that being said, I’ve been to many French territories around the world and it’s probably the least French territory I’ve been to, simply because of the influent from the Dutch side, a lot of people will speak English in their day-to-day business. The French side of the island is probably, like I said, I think a little nicer, may be a little less touristy, a little less developed in the Dutch side. Dutch side has the majority of the population, even though it’s a slightly smaller area and it’s more developed. You’re going to see more large resort on the Dutch side, also strip clubs, bars, things like that.

Chris: So a lot of the places we’re talking about have beaches, but we’re going to talk some of the islands who really have none. What else is going to draw … so you mentioned the culture, are there particular things that you would recommend that we do while we’re in Saint Martin?

Gary: I think the unique thing about Saint Martin is its airport and runway butts right to a beach called Maho Beach. You can be on the beach and have planes flying right over your head. If you do a search on just Saint Martin airport or something and watch some of the YouTube videos, you’ll see some incredible videos of people being blown over by jet engines, so actually I went and did that. The bars on the beach will have time schedules of when flights are taking off. Usually, I want to be there may be 15 minutes or even 20 minutes before when they arrive, but they will come very, very low right over your head. When they take off, especially the very large jets that are flying to Europe, they will blow an enormous amount of thrust right in your face and kick up a ton of sand and it’s something to experience. I think most people may have flown on a jet before, but you’ve never really experienced viscerally how powerful a jet engine is until you’ve stood behind one.

Chris: Despite the fact that we have done this whole show before, I’m still amused by the fact that you’re recommending that we go sit on a beach and get blown out by jet engine drill.

Gary: There’s a road that runs between the runway and the beach. You probably don’t want to stand on the road and grab the chain-link fence, which people do and you could blown over, you don’t want to do that. If you’re just standing on the beach, it’s basically just going to be a lot of wind and it’s going to kick up some sands, you don’t want to cover your eyes, but yeah. It’s actually become one of the largest attractions for people visiting from a cruise ship to do that. I think a lot of it is because of the success and the notoriety it’s gained on YouTube that people want to experience at firsthand.

Chris: You mentioned cruise ships. You have been on cruise ships before, but aren’t the biggest fan of cruise ships. Not that you hate them, but …

Gary: No, it’s not my thing. My biggest problem with cruise ships is always what you do in port, especially if you don’t have time.

Chris: But you came back a little different experience from the Caribbean in cruise ships.

Gary: These are very small islands and many of these islands you can actually go around the entire island in approximately an hour, which means you have plenty of time to stop, see some sites, go to a museum, have some lunch, take some pictures, and get a reasonably thorough experience on many of these islands because they’re so small and so you have eight hours or 10 hours or something like that. You can get then in a good den in many of these islands and have an experience that you’re not going to have if you’re trying to see Rome in eight hours.

Chris: Right, sure. The other thing too is you don’t have that far to go.

Gary: So example, if a cruise ship stops in Saint Martin, they stop in Philipsburg and you’re right downtown immediately. You don’t take a bus, anywhere you could just walk right off the ship and spend an enjoyable day in Philipsburg, lots of shopping, lots of restaurants and you’ll never have to even get in a car.

Chris: We say lots of shopping. I think of the shops that tend to cater the cruise ships tend to be more high-end shopping.

Gary: Yeah, lots of jewelry stores, things like that, kind of the typical stuff you see everywhere that cruise ship stopped.

Chris: Anything else about Saint Martin before we head out?

Gary: I just think that the dichotomy between the French and the Dutch side in entrusting. There are many things that are similar, but many things are different. I think if you visit Saint Martin, whatever side you’re going to, make sure that this is the other side as well just to see the differences between the two sides.

Chris: Okay, and where there do we go from here?

Gary: The next island I visited would be the island of Anguilla, which is very close to Saint Martin. The ferry from Saint Martin to Anguilla is about 15 to 20 minutes. It’s a very short ferry ride. There is a ferry terminal for Anguilla about five minutes from the airport, so it’s very short trip. If you buy a ferry ticket, they will usually include the transportation from the airport to the ferry terminal as part of the ticket. They have an immigration facility at the ferry terminal for leaving Saint Martin, so it’s a very short trip.
What’s unique about Anguilla is that it is not a volcanic island, whereas most of the islands in the Caribbean are. It is a raised coral reef, which has two implications. One is that there are no high points on the island. The entire island is incredibly flat. The second thing is you have a lot of white sand beaches and that’s really its highlight. They had by far I think the best beaches I’ve seen anywhere in the Caribbean and they had many of them. They’re very proud of their beaches.
Anguilla is a British territory still. Interesting bit of history is that there was a thing called the Anguilla Revolution fought in 1968, and by fought in using that word very loosely. Prior to independence, the British created a territory called St. Kitts-Nevis in Anguilla. The problem is Anguilla didn’t really want to be a part of it. They felt that the people from St. Kitts were keeping all the money, so one day they rounded up all the police officers who are all from St. Kitts and put them on airplane and said goodbye. They declared their independence, which lasted a couple of days before the British came back and re-colonized them and that’s where they are today.

Chris: My impression from one we talked before was that Anguilla also doesn’t get as much tourism despite having these beautiful beaches.

Gary: Not really. They said that get about 28,000 visitors a year, which is higher than the population of the island, much less than many of the neighboring islands. Part of this is because you don’t see as many flights coming to Anguilla. Usually, if you fly to Anguilla, you have to fly into Saint Martin and then take the boat ride. Even though those are very boat trip and it’s very fast and very easy that extra step is what hurts tourism to a lot of these smaller islands because it isn’t just a direct flight. A lot of people prefer the direct flight, you get off, go to your resort and you’re done.

Chris: Was it any cheaper because there is less tourism?

Gary: Not really. Anguilla is considered to be the second most expensive island in the group after Saint Barts. I don’t think that it’s quite as … it is not nearly as bad as St. Barts and they have should any chain of hotels in Anguilla so there’s no Radissons or Marriotts or Hyatts or things like that. They’re all rather independent and they do have several very upscale hotels, but they also have a fair number of smaller hotels as well. The cost of the room I had, I believe it was called the Frangipani Hotel, it was approximately $100 a night and it was on a white sand beach in the low season.

Chris: Which does not sound that expensive to me.

Gary: No. I’m sure it would be more than that during the high season.

Chris: Oh, sure right. Excellent. Actually, what we’re talking about cost of food though is one thing you found to be fairly expensive.

Gary: Yeah. Everywhere in the Caribbean, I found food to be rather pricy. Especially in a place like Anguilla, they basically grow nothing. It’s a very dry island, horrible agriculture. They rely very heavily on tourism, which means a pretty much older food is important. I called it an island tax, which is not a literal tax. It’s just the extra cost for shipping everything in.

Chris: I’m going to guess too that they have to desalinate a lot of their water.

Gary: For some of the resorts, I’m sure they do that. But for most homes you’ll see in the Caribbean, they will have rainwater.

Chris: Oh, like Bermuda then, okay.

Gary: Say but your house is actually built on a cistern. You build a cistern first, build the house over it, and then that just fills up from rainwater.

Chris: I know in Bermuda where they have this similar thing as very, very dry. They have the white-painted roofs, which look very pretty in the pictures, but what they’re really for is capturing rainwater.

Gary: You’ll see that in most places. You’ll have either a cistern outside the house or system that captures much of that as possible. For the most part that works occasionally, you’ll have a drought where they don’t get a lot of rain. That’s usually what they do.

Chris: Anything else about Anguilla?

Gary: Like I said, great beaches. If you’re a beach person and you don’t want the huge crowds, I think Anguilla is a great option. Again, has the reputation of being more expensive than Saint Martin, but I didn’t find it to be crazy at rate as expensive like I found in places like Saint Bats or Tahiti.

Chris: Did you have a favorite beach in Anguilla?

Gary: There was one place we stopped at that had been voted one of the best beaches by, I think it was Conde Nast Magazine. Shoal Bay was where I was staying and the other beach was Savanna Bay, I think. They’re all white sand, very fine grain, and very broad, not just a very narrow beach so you had a lot of sand distance from the start of the sand to the water.

Chris: Excellent, and not a lot of low-flying airplanes either.

Gary: No.

Chris: Where do we go next?

Gary: My next stop was the island of Saba, which I’m guessing most people have heard of Anguilla, they’ve heard of Saint Martin, they’ve herd of St. Barts, and most of them probably haven’t heard of Saba, which is too bad because I think in many respects it’s the most fascinating island in the Caribbean. It is a Dutch island, not a Dutch territory. It is a part of the Netherlands. With the dissolution of the Netherlands Antilles in 2010, Saba, St. Eustatius, and Bonaire are municipalities of the Netherlands. If you look at the map of the Netherlands, it will have those three small islands as part of the Netherlands, as the same way that Hawaii is part of the United States. The [highest 00:20:19] point in the Netherlands as a trivia question is on the island of Saba, not in Europe.

Chris: You climbed to the highest point of Netherlands, I believe.

Gary: I did. It’s called Mt. Scenery. The living situation of things on Saba is really unique. There’s road naming situation of things in Saba is really unique. There’s road that goes through the island. It was built I think from the ’60s to the ’80s. No one thought it could be done, because it’s so mountainous called The Road. The capital is located in the bottom of a volcanic caldera, it is called The Bottom. The village on the west side of the island or the windward side of the island is called Windward Side, so it’s all pretty simple naming.
The key to Saba is that there’s 2,000 people live in the island and it’s very mountainous and it seemed like all of our transportation, wherever we were going, was up and down. It’s all vertical, because everything … the airport in on one end of the island, the port is on the total other side of the island, just getting everywhere involves curving roads, lot of hairpin turns and it’s very remarkable that people were able to live there.

Chris: There are not a lot of people, as you were pointing out.

Gary: The airport has the distinction of having the world’s shortest commercial runway. The only flights there are from Saint Martin. It’s a 12-minute flight and the pilots have to be especially trained in order to land because it’s so short.

Chris: When you’re going to Saba, you’re going to see the scenery mostly, because no beaches.

Gary: There is one sort of tiny rocky beach near the airport. That’s about it, certainly nothing to write home about. Yeah, you go there because beautiful landscape. If you like hiking, fantastic place to hike, lots of trails that go up the mountains and around the mountains, and also some interesting scuba diving as well. I did one dive there. I actually got to see some volcanic sand at the bottom of the sea that was quite hot when you touch it.

Chris: Oh, interesting, huh?

Gary: There’s active volcanism going on in the region and you can tell it when you do the dive.

Chris: You’re a diver as you point out. Did you do a lot of diving in the various islands?

Gary: Not as much as I would like. I only really dove in Saba and then I did a dive earlier in the trip in the Bahamas, which isn’t really part of the discussion for this. Hope to go back to some of these places and do more diving.

Chris: Anything else about Saba?

Gary: If you’re going to be in Saint Martin, I highly recommend a visit to Saba. It’s a short flight, not necessarily a cheap flight. There’s also a ferry that goes to Saba. It’s about a 90-minute ferry ride. Even if you’re there for the day or you just want to spend one night there, it’s just a really interesting place. The first language of the people there is English, although pretty much everyone speaks Dutch, very different accents that they had. It was almost like a pseudo-Bostonian accent with a bit of an English accent thrown in, very unique. They use US dollars and so even though as part of the Netherlands it has a very different feel not very Dutch at all.

Chris: I almost got the impression that a smaller version of the trip to Judea would be just two or three islands we talked about so far, do Saint Martin, do Anguilla for the beaches, and do Saba.

Gary: Yeah. After Saint Martin, there are four islands which are easily connected either by ferry or by air to Saint Martin. Those we’ve discussed, Anguilla and Saba, the other two being St. Eustatius and St. Barts. You could visit all those islands easily from Saint Martin and that would be a very doable trip, regular ferry service, very short flights.

Chris: That sounds like that would be a two-week trip or something like that minimum [to figure out through 00:24:00] and all that.

Gary: Yeah, you could probably do it in maybe less than that, 10 days. Like I said, some of these islands aren’t big. St. Barts, depending on your budget, probably you don’t want [inaudible 00:24:08], but certainly worth the day trip.

Chris: Let’s talk about St. Barts. We referred to it a couple of different times. It is the most expensive island in the Caribbean. It has that reputation.

Gary: Technically speaking, in the whole Caribbean, I believe the island of Mustique in the Grenadines is actually more expensive, because everything is private villas, priced at like $10,000 a night for the average wealthy person. That’s for the billionaire wealthy person. This is just for the regular millionaire class type. St. Barts would definitely be the most expensive island certainly in the Leeward Islands.

Chris: When we say expensive, can we put some numbers on that?

Gary: I did not stay overnight. I only did a day trip, because I could not find a place for under $350 a night and this was during the low season.

Chris: In the high season, I think you said we’re talking more like $1,000 a night.

Gary: Certainly, during like the Christmas-New Year week that time, yeah, you’re probably going to be paying something around that.

Chris: Why would someone go to St. Barts?

Gary: To say that they went to St. Barts.

Chris: To see all the other people go to St. Barts I think is the other answer.

Gary: I think it’s like going to Bora Bora or Saint-Tropez or any other high-end destination. These places have developed a reputation as being high-end and it’s a self-fulfilling thing. They attract high-end people, high-en hotels, and it just feeds off itself.

Chris: Did you have any celebrity-spotting experiences in St. Barts?

Gary: I did not. In fact, this fitted advice I can give people. If you do want to go to a day trip to St. Barts, which is a good idea, don’t do it on a Sunday because everything was closed. The capital, Gustavia, interesting place. I was able to spend several hours walking around, went to a cafe, but for the most part you can be bear off going on a weekday I think.

Chris: Then we have one more island in that cluster.

Gary: St. Eustatius, which along with Saba is part of the Netherlands. They’re often grouped together. However, the islands couldn’t be more different. Saba, the population tends to be more European decent; St. Eustatius, almost all Afro-Caribbean. At St. Eustatius, there are two peaks on either side of the island, but they’re not that big so a very broad valley in the middle where pretty much everyone lives. A very historic island, so you can see in Fort Oranje, which is still standing. It used to be the most important port in the Caribbean, St. Eustatius. It was called The Golden Rock; it was some port.
It has changed names 22 times between various European powers, the last one to have it were the Dutch which is why it’s a Dutch island today. On the shore, you can still see all the warehouses made of stone and everything else. It used to be a seawall that the Dutch built to keep the sea out so they have a little bit more land, because the Dutch are really good at that. To this day, its primary industry there’s an oil storage facility, so the big tankers will come, dump off oil here. They hold it in that area then smaller ships take it to other islands.

Chris: You mentioned historic, there’s a significance for St. Eustatius relative to those from the U.S.

Gary: Yes. In November of 1776, the Dutch governor of St. Eustatius fired a cannon salute at the USS Andrew Doria, marking the very first time in other country recognized an independent United States. They were one of the primary sources of weapons for the rebel forces fighting the British at the time, and it so angered the British, they invaded the island and took it over.

Chris: You happened to be there on the Fourth of July.

Gary: Yeah. The airport in St. Eustatius is named after Franklin Delano Roosevelt, who visited in, I want to say 1936, might be off by a few years. He dedicated a plaque at Forth Oranjestad which acknowledged the first salute. There’s a couple of other plaques given by I think a veteran of Foreign Wars Organization and the Daughters of the American Revolution Group that acknowledged it as well.

Chris: Excellent.

Gary: St. Eustatius does not get a lot of tourism and there’s only about two hotels in the entire island, and like Saba, you do not have much in the way of beaches.

Chris: We talked about St. Barts being if you really are somebody who wants to drop a load of money, go to St. Bart. Is there an opposite if you’re a backpacker and you want to go to the Caribbean? Is there a place you can go or should go in these islands?

Gary: Not really. The only hostel I saw was on the island of Guadeloupe, which is a French territory. They had dorm beds and things like that and that is the only place I found in the entire Leeward Islands that had something like that. You can certainly stay a bit cheaper in some of the hotels. Like St. Eustatius, I would not say as high-end at all. It was a very nice place to visit, but it’s not backpacker cheap. I don’t think [inaudible 00:29:02] should be considered that cheap.

Chris: You mentioned being a historic place. Anything interesting particularly the sea besides … you mentioned the Fort Oranjestad.

Gary: Yeah. That’s pretty much the biggest thing. A representative from the tourism board, they gave me a tour of the island. I think the whole thing is like a half hour. We went to one side, we drove to the end of the road and we take the other side to another end of the road and that was it. There wasn’t much else to see. The roads didn’t really go anywhere else.
There is a volcanic cone on the island and you can climb that. It’s called Mt. Quill, q-u-i-l-l, but I didn’t do that during my stay. [Inaudible 00:29:44] climb right down into the cone, which they told me is very, very green and very lush.

Chris: You mentioned that this island is very green and when you talked about the island of Anguilla being very dry, so basically the taller islands are green or at least have a windward side that is greener.

Gary: Catch a lot of the clouds, so when I hiked to the top of Mt. Scenery on Saba, the last third of the climb was all in clouds basically, which actually meant that walking around is quite slippery and it was much more difficult to get down than it was to get up. I think I slipped about six times on the way down.

Chris: I remember being surprised when I was in the Virgin Islands, because I’m used to going to the islands like in Hawaii where everything is or at least part of the island tends to be fairly lush and all the islands have fair amount of height. There’s mountains on a lot of the different islands and the Virgin Islands were very, very dry in comparison. They were not my picture of a tropical island, I guess.

Gary: Yeah. When you get to some of the islands, like Aruba, that’s very dry mostly cactuses in fact.

Chris: Where do we go next?

Gary: From here, we fly to the island of St. Kitts. St. Kitts and Nevis is the newest and smallest independent country in the Western Hemisphere. Despite being small, I think the total population of the country is about 55,000. It is a federation so each island, St. Kitts and Nevis, run their own show. A couple of years ago, there’s actually an independence referendum on Nevis, which has a population of I think 12,000 to 15,000, somewhere around there. They needed the two-thirds majority to secede and they were only like less than 100 votes away from doing it. We could have even a smaller country in our backyard had that gone through.

Chris: Let’s start with St. Kitts. What does St. Kitts like?

Gary: St. Kitts is called the Mother Colony. It is the location of both the First French and English colonies in the Caribbean, so they both started on St. Kitts so had the reputation. You can go there and see Brimstone Fortress, which is a UNESCO World Heritage Site, the only one in the Leeward Islands. It was called The Gibaltar of the Caribbean. It’s still there today, still standing, abandoned in the early 19th century, but since independence they fixed it up and now it’s probably the single largest attraction on the island.

Chris: What drew both the French and the English to the island?

Gary: I don’t know.

Chris: Okay. I can get the fact that the Cuban, Espanol, and Puerto Rico were settled by the French because they got there first, but that left some of the small islands, but I wasn’t sure if there was a particularly obvious reason why St. Kitts would be colonized next.

Gary: If you look at it on a map, it’s shaped like a guitar and so the area around the neck of the guitar would probably be the location for the best port, but that’s all mountainous and you can’t really get there. A place like Antigua, I thought it makes much more sense for naval vessels, because it’s such an irregular coastline and there are plenty of very good harbors that are available. In fact, that’s where Lord Nelson harbored many of his ships in Antigua. With St. Kitts, I would say it’s probably the least developed island that I visited, because they’re not a territory of anyone anymore; they’re independent. They have a fair amount of tourism. They have a unique policy that allows people to buy citizenship if you want. I think for $120,000 you can get a St. Kitts passport.

Chris: Really?

Gary: Yeah. You can just [flight up 00:33:23] buy citizenship. I think if you make a $400,000 investment, so if you buy property, you can get citizenship as well. I saw a couple of signs at the beginning of the neck of the guitar part of the island is where you see a lot of the higher-end developments, the expats, things like that, some of the nicer hotels. You’ll see signs that say, “This investment in this condo qualifies for citizenship,” things like that.

Chris: I assumed they’ll do that in part for tax-shelter reasons or things like.

Gary: Just having a second passport. I think that if you are citizen of St. Kitts, you can pretty much travel to most other commonwealth countries without a visa, so it’s not a bad deal. I don’t know how many people have taken advantage of it, but it’s a unique offer. I think Dominica as well in the Windward Islands offers a very similar thing.

Chris: Interesting.

Gary: I should also note the island on Nevis, which is the sister island, that’s a 45-minute ferry ride. They leave several times a day. Several high-end hotels on Nevis, so there’s a Four Seasons. I believe that Travel & Leisure Magazine recently came out their top 50 hotels in the world and two of them were on Nevis. To give you an idea, Alexander Hamilton is a native of Nevis. He’s a Nevisian, not a Kittitian, which are the names of the people in the respected islands. The Alexander Hamilton house is still available and not far from the port in Charlestown, which is the capital of Nevis.

Chris: Excellent. What else is there to see besides the Alexander Hamilton house in Nevis?

Gary: There are some more beaches on Nevis that you’re going to see on some of the other islands I have previously mentioned. For a lot of these, it’s not that there’s necessarily unique stuff. It’s a place to come and get away from things. Nevis, again, does not get a ton of tourism. A lot of people don’t know where it is or they’ve never heard of it, which I think is why you have several high-end hotels that are not opening there. The beaches are sufficient and it’s not crazy difficult to get to. If you had like a private jet or something, you can land on Nevis, so it wouldn’t surprise me if you see even more development in the future.

Chris: Actually, I think what you said that was fairly important so when we talk about this region this isn’t necessarily the region for people who want to do something every hour of every day.

Gary: Things are pretty laid back. I think any island you go to you make what island time and taking life easy. On these islands, there’s not a lot of area, there’s not a lot of space. The things which are of historical significance may not be that big of a deal in the big scheme of things. It could be a farm or a quarry or something like that or just an old church. You could probably see a lot of the historical things on a day tour of an island and that may take no more than may be four or five hours.

Chris: And then we’ve got at least one more island.

Gary: Two, may be three, depending on how you define it. From St. Kitts, I flew to the island of Antigua. Antigua population I think it’s about 80,000, so a little bit bigger, and very interesting island. It’s Antigua and Barbuda is the name of the country, an independent country. The island of Antigua has a very irregular shape coastline, lots of inlets, lots of harbors and bays. It was used as the primary British naval base for quite a while. Some excellent cricketers have come out of Antigua, Viv Richards; I found because I asked who Viv Richards was at a restaurant, because they got a poster of him on the wall; from Antigua, considered one of the al-time great cricketers.
The airport there is slightly larger so it can take direct flights from Europe and from the United States, so it tends to get a bit more tourism than what you have on some of the other smaller islands that I’ve mentioned. While it is mountainous, it is not nearly as mountainous as some of the other islands. There’s a very broad plain, which means that it can support a higher population which it does.

Chris: You mentioned you learned about Viv Richards. My impression from that story was that they were stunned that you didn’t already know who he was.

Gary: Yeah, and he’s like Babe Ruth for the West Indies. For those of you who aren’t familiar with cricket, the national game this country versus that country is I’d say the oldest and probably the biggest thing in cricket, and most of the Caribbean cricket countries play under one team, so that’s the West Indies. That would include primarily Jamaica, Trinidad, Guyana, Barbados and then many of the smaller islands such as Antigua, St. Kitts, Nevis, et cetera. I think Nevis that they had one player on the team, Antigua had several, St. Kitts had none, but it changes all the time as new players come up.
In the sister island, Barbuda, I really wanted to go Barbuda but I wasn’t able to do it on this trip. But 95% of the population in Antigua and Barbuda live in Antigua. Barbuda has only I think 5,000 people. There’s a two-hour ferry that does go from Antigua to Barbuda that leaves daily; once there, once back. Barbuda is not volcanic. It is a raised coral reef similar to Anguilla and so you’ll see a lot more beaches even though it does not get nearly as much tourism as Antigua does.

Chris: Then that leaves Montserrat.

Gary: Yes. Montserrat is a British territory and it is probably best known for the volcanic eruption which took place in the late ’90s. The capital of Montserrat … at the time of the eruption, Montserrat had a population of approximately 12,000 people. The capital of Plymouth was basically wiped out by a pyroclastic flow, which came off the volcano, buried the city. Today roughly, I’d say more than half of the island is out of balance for humans. You’re not allowed to visit. There are no roads anymore and about two-thirds of the population ended up leaving the island. Some of them went to neighboring islands, such as St. Kitts and Antigua, and others just went to the UK.

Chris: When we say not allowed to visit, because they’re deemed unsafe.

Gary: Correct. Actually, I don’t even know if you … they may have some dirt roads or things are available through off-roading, but there are no more paved roads available to get to these places. They’ve all been buried.

Chris: You didn’t do but you can do a helicopter tour of Plymouth.

Gary: Yes. There are helicopter tours from Antigua which are available and you can do that in a day trip. You leave from Antigua and flies to Montserrat. You fly over the ruins of Plymouth. I think they have launch or something and then fly back. There are boat tours that are available that go off the coast of Plymouth, but you cannot actually go to Plymouth itself. You can go to the Montserrat volcanic observatory, which is probably the biggest attraction on the island, and it’s a great viewing point for the volcano itself. As late as May of 2013, there was lava still coming out of the volcano so it’s quite active, and they’re pretty sure that they’re going to see more of the same … still some rather violent eruptions which is why they’ve cordoned off so much of the island. In the previous eruption, several people died because they simply ignored instructions and wanted to stay in their home. Similar to what happened in the United States with Mount St. Helens.

Chris: Last time you were on, we did this before. I asked you who the most interesting person you met in your trip was and you mentioned someone from Montserrat.

Gary: Yeah, my cab driver. I got off the ferry. I took a ferry from Anguilla, arrived late at night and the hotel … and I should say there are no hotels that I found that were actually on any of the booking engines, like Expedia or I actually had to go online, find the name of a hotel, send them an email, get confirmation in that way and they said, “Oh, yeah. Moose will pick you up.” So I’m waiting for this Moose to pick me up and eventually I was waiting and someone said, “You arrived?” I said, “Yeah. There’s a guy named Moose, who supposed to pick me up,” and the guy, “Oh, Moose. He’s over there.”
He was with a bunch of people drinking and Moose was pretty much my guide for the three days I was on Montserrat. He took me to the hotel, drove me around, showed me all the sites. He lived in Plymouth so his home was destroyed. He told me his children now live in London and they go to school, but he intends to stay on Montserrat, doesn’t want to leave. He got the nickname Moose, because he used to be a body builder and was on the cover of building magazines I guess.

Chris: Excellent.

Gary: Montserrat has also one of these crazy Leeward Island airports that is somehow chiseled into the stone and so it’ very, very short runway. The only flights there are from Antigua, so that’s the only way you’re going to be able to fly to Montserrat.

Chris: What warning you would give about going to the Leeward Islands?

Gary: It isn’t cheap and the transportation can sometimes be rather difficult. One question I constantly get is that people envisioned traveling these islands by boat. In the islands we’ve talked about in the show, it is possible. In a group round Saint Martin it’s very easy. However, getting to St. Kitts is very difficult. The only way I found to do it is that there’s a once-a-week ferry that goes from Nevis to Montserrat and then there are regular ferries from Antigua to Montserrat. If you use that ferry, you could divide the Leeward Islands into two groups, the Saint Martin group and then the St. Kitts-Antigua-Montserrat group. So you could travel by boat in those places, but getting between St. Eustatius and St. Kitts you need a yacht or something like that.

Chris: I know that in the nearby Virgin Islands that there is a rental yacht thing is fairly easy to do. There are a number of companies that will do that there and it’s fairly common. Is that common in this area as well?

Gary: I did see people that did it. I met one guy who is a CEO of a travel company I met up with and his family was a renting a chartered yacht and basically spending a year sailing through the Caribbean. It certainly can be done. Knowing absolutely nothing about captaining a ship, I would never think of it. The distances between the islands are quite short, so it’s going to be less than a day probably, may be sometimes much, much less than a day to go between the islands. Especially if it was motorized or something and the weather was good, you could just go from harbor to harbor to harbor and do it that way.

Chris: Okay.

Gary: One other thing I should mention is that the island of Guadeloupe is sometimes listed as one of the Leeward Islands and sometimes it’s listed as a Windward Island. Guadeloupe is the largest island in this entire chain. It’s very different from everything else. It’s a French island. I was in Guadeloupe for three days. But quite frankly I didn’t get to explore a lot of the island. I pretty much vegged out and rested.

Chris: You are a photographer, increasingly wonderful photographer I would have to say, especially when I consider how your photography has changed over the number of years you’ve been coming back on the Amateur Traveler. You’re standing in the prettiest spot in the Leeward Islands. Where are you standing? What are you looking at?

Gary: I took some really nice photos on Saba up on Mt. Scenery. In fact, as we’re recording this and I put up a wall paper on my website every month and this month wallpaper is from the island of Saba, just a picture of a wooden bench that was sitting in the rainforest that I took a picture of and I enjoyed it. You’re going to get those sort of views on Saba. The beaches in Anguilla, always people love the beach photos. I have several photos of the white sand beach and the palm thatched parasol that people can sit under, those kind of things. I think those are some of really stereotypical views you’re going to get. Basically, most of the islands are volcanic islands with a lot of green. If you would take an aerial view, you’re going to get something like that on pretty much every island.

Chris: Since we’re talking about Gary’s photography, I will give a plug here that you are now doing photography tours. If people wanted to learn how to take pictures more like the wonderful pictures they see on your site, where’s your next one?

Gary: We haven’t announced it yet, but I hope to announce it within the next month. Last year, we went to Italy. The year before, we did one in the U.S. Southwest. We think we have a location pick out, we haven’t finalized it yet, but we’re going to be announcing it soon.

Chris: Excellent. And “we” there being you and G Adventures.

Gary: G Adventures, this is my sponsor and they handle the logistics. I don’t want to be in the tour business and they do a pretty good job of it.

Chris: Excellent. What did you find were the best resources for planning a trip to this area, besides Amy, who does a lot of your travel coordination?

Gary: General Google searches, because for some of the islands it’s very trivial. Finding things on Antigua and Saint Martin was not hard at all, even in Anguilla places like that. Places like Saba, St. Eustatius or Montserrat was rather difficult, because they don’t have normal hotels. They’re not tied into the booking system so we have to some research. Sometimes you’ll find people just giving comments on trip adviser, not necessarily reviews of hotels but just what to do on the island or things to see and who to talk to.

Chris: Three more questions. What else should we tell people before I get to my last three questions?

Gary: That in and out of itself would be a question.

Chris: All right.

Gary: If you’re going to visit the region, I highly recommend not just visiting one island whatever that might be. If you’re going to visit Saint Martin, take the time to visit Anguilla or Saba or St. Eustatius, because these are wonderful little islands that get very few visitors and they have a very different feel from what you’re going to get in the tourist areas of, say, Saint Martin.

Chris: Last three questions. One thing that makes you laugh and say only in the Leeward Islands of the Lesser Antilles.

Gary: Many of the islands, not on Saint Martin, they print their own license plates. By printing their license plate I mean anybody can print their license plate, so license plates are different fonts, different colors. We’re accustomed to a standardized plate for a U.S. state or a country. Same, no. They don’t bother to print their license plates because there aren’t many cars, so you just go to a place and they print like a vinyl license plate, however, what style you want and they put it on their car. I had never seen that before anywhere in the world, but [inaudible 00:47:50] do that.

Chris: I’ve never heard of that either; interesting. Finish this sentence: You really know you’re in the Lesser Antilles and the Leeward Islands when what?

Gary: You find yourself filling out several customs forms every time you go between islands, every little island. Even if you’re going from Dutch Saint Martin to Dutch Saba, you got to fill out a customs form. You got to get your passport checked every single time and that’s the biggest downside I think to traveling in the region.

Chris: If you had to summarize the region in three words?

Gary: Small, mountainous, really small.

Chris: Gary, we’ve mentioned a couple of times already. Where else can people find you on the internet?

Gary: Oh, I’m all over the internet. They can find me on Twitter, @EverywhereTrip. I’m on Facebook, search for Everything-Everywhere. I’m on Instagram. I’m on Google Plus.

Chris: Don’t you also do an award-winning travel show on the internet?

Gary: I do, but I’m really just carried by my co-host.

Chris: For those of you who don’t know, Gary and I are, oh what, 200 episodes into This Week in Travel, which is more of a travel news and interview show, so not a destination show, a little different than Amateur Traveler, a fine show though.
Excellent. Gary thanks so much for coming back on and we’ll have Gary on soon to talk about the Windward Islands as well.

Gary: Thanks for having me.

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Chris Christensen

by Chris Christensen

Chris Christensen is the creator of the Amateur Traveler blog and podcast. He has been a travel creator since 2005 and has won awards including being named the "Best Independent Travel Journalist" by Travel+Leisure Magazine.

2 Responses to “Travel to the Leeward Islands of the Lesser Antilles in the Caribbean – Episode 386”



Beautiful place)



It’s very funny that I read found this post by accident while planning my next trip to the Leeward islands! I hope they are really as amazing as they seem. 🙂

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